Sodium hydride → HCID 21830402, compound

HRID 1601050Notes

Reaction equation

HRID 1601050 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])[CH3:3].[H-].[Na+].Br[CH2:19][C:20]1[CH:21]=[C:22]([CH:30]=[CH:31][C:32]=1[N+:33]([O-:35])=[O:34])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]>CN(C=O)C>[C:2]([O:5][C:6]([N:8]([CH2:19][C:20]1[CH:21]=[C:22]([CH:30]=[CH:31][C:32]=1[N+:33]([O-:35])=[O:34])[C:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:1])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 279800Di-tert-butyl IminodicarboxylateHCID 10335882Tert-butyl 3-(bromomethyl)-4-nitrobenzoate

Product 1

HCID 21830402HCID 21830402, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Di-tert-butyliminodicarboxylate (4.35 g, 20.0 mmol) was added to a suspension of sodium hydride (0.48 g, 20.0 mmol) in anhydrous DMF (30 mL) at RT. After 30 minutes, a solution of t-butyl 3-bromomethyl-4-nitrobenzoate (6.3 g, 20 mmol) in DMF (15 mL) was added rapidly dropwise. After 16 h, the solvent was evaporated and the residue partitioned between EtOAc (200 mL) and water (40 mL). The organic layer was extracted with water (3×50 mL) and brine (40 mL) and dried finally over Na2SO4. Removal of solvent gave the crude product which was purified on flash chromatography (15:85; EtOAc:Hexane) to give the title compound (81.5%): MS (ES) m/e 453 (M+H)+ ; 1H NMR (400 MHz, CDCl3) δ 7.97-8.10 (m, 3H), 5.16 (s, 2H), 1.62 (s, 9H), 1.49 (s, 18H).

Workup

  1. waitAfter 16 h
  2. customthe solvent was evaporated
  3. customthe residue partitioned between EtOAc (200 mL) and water (40 mL)
  4. extractionThe organic layer was extracted with water (3×50 mL) and brine (40 mL)
  5. dry with materialdried finally over Na2SO4
  6. customRemoval of solvent
  7. customgave the crude product which
  8. customwas purified on flash chromatography (15:85; EtOAc:Hexane)

Sources & evidence

ORD record
ord-42947e91303f49b08b99174c15900a5e
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

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